Hydrazine → HCID 178454991, compound

HRID 2405897Notes

Reaction equation

[Si:1]([C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10]([C:16]([C:18]2[C:19]([Cl:25])=[N:20][CH:21]=[N:22][C:23]=2Cl)=O)[C:9]=1[F:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:27][NH2:28]>C1COCC1.O.CCOC(C)=O>[Si:1]([C:8]1[C:13]([F:14])=[C:12]([F:15])[N:11]=[C:10]([C:16]2[C:18]3[C:23](=[N:22][CH:21]=[N:20][C:19]=3[Cl:25])[NH:28][N:27]=2)[C:9]=1[F:26])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -50 °C

Procedure

[4-[tert-butyl(dimethyl)silyl]-3,5,6-trifluoro-2-pyridyl]-(4,6-dichloropyrimidin-5-yl)methanone (901 mg, 2.13 mmol) was dissolved in THF (18 mL) and cooled to −50° C. Hydrazine (1M in THF) (2.20 mL of 1 M, 2.20 mmol) was added dropwise over 10 minutes. The reaction mixture was stirred at this temperature for 30 minutes and then allowed to warm to ambient temperature for 30 minutes. The reaction mixture was diluted with water and EtOAc. The organic layer was separated, washed with water (2×), brine, dried (MgSO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (ISCO Companion™, 80 g column, eluting with 0-3% MeOH/DCM) to give the sub title compound as an orange foam (498 mg, 58.4% Yield). H1 NMR (400 MHz, DMSO) δ 15.04 (1H, s), 8.92 (1H, s), 0.95 (9H, s) and 0.44 (6H, s).

Workup

temperatureto warm to ambient temperature for 30 minutes
customThe organic layer was separated
washwashed with water (2×), brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude mixture was purified by column chromatography (ISCO Companion™, 80 g column, eluting with 0-3% MeOH/DCM)

Sources & evidence

ORD record: ord-085629f80f664abe8e1455d84ac5056f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809335B2

Reaction notes

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